That's what we'll be doing too. We'll wear our heaviest footwear on the plane too. It's a bit odd, coming from Florida and dressed for Alaska. LOL. Well, Vancouver anyway. The heavier jacket (coat in my case) will be the pillow or cover. Planes can be chilly even for Florida residents.
My concern is "tops." I change my shirt daily, and do NOT want to have to bring enough shirts, one for each day. On the other hand, I so do not want to do laundry. I'm going to have to see what I can come up with to compensate for this "need." LOL.
We have a couple turtlenecks, a couple long sleeve tee style shirts, true winter sweaters (those great ones that we couldn't bear to part with when we moved to Florida) the warm coats... hiking style boots, scarves (mine is more a pareo thing, as I use it for other purposes too) ...
Trying hard to keep things to a minimum! Not easy to do!